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Ch01.ppt dr. suzan


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Organic Chemistry

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Ch01.ppt dr. suzan

  1. 1. Organic Chemistry CHEM 230 1
  2. 2. ‫معلومات عن أستاذة المقرر‬ ‫السم : د. سوزان عبدالرحمن خياط‬ ‫أستاذ الكيمياء العضوية المشارك‬ ‫قسم الكيمياء‬ ‫كلية العلوم )فرع الفيصلية( – جامعة الملك عبدالعزيز‬ ‫غرفة رقم ‪ 314A‬الدور الثاني – 901 ‪ C‬الدور الرضي‬ ‫البريد اللكتروني ‪‬‬ ‫‪‬‬ ‫اكلموقع الكلكتروني ‪‬‬‫2‬
  3. 3. No. of Units .Course No ‫عدد الوحدات‬ Course Title Pre-requisites 11 ‫رمز ورقم‬ ‫اسم المقرر‬ .Th .Pr Credit ‫المتطلب السابق‬ ‫المقرر‬ ‫النظري‬ ‫العملي‬ ‫المعتمدة‬ Principals of Organic Chemistry I CHEM 230 3 3 4 CHEM 110 ‫الكيمياء العضوية لغير طل ب الكيمياء‬ :‫أهداف المقرر‬ ‫يهدف هذا المقرر إلى إعطاء الطالب الذي ل ينوي التخصص في الكيمياء أسس الكيمياء العضوية وبعض تطبيقاتها الهامة‬ Course Objectives: Giving the theoretical and experimental basis of organic chemistry for non-chemistry students :‫المحتوى العلمي للمقرر‬ :‫ويشتمل المقرر على‬ - ‫دراسة الربط الكيميائي في المركبات العضوية من خل ل نظرية التهجين - تقسيم المركبات العضوية حسب المجموعة الوظيفية‬ ‫تسمية المركبات العضوية - التشكل - التفاعلت الكيميائية - المركبات الحلقية غير المتجانسة – السكريات - الحماض المينية‬ ‫والبروتينات - التربينات -تطبيقات المركبات العضوية في الطب والزراعة والتغذية والصناعة‬ Course Descriptions:Study the chemical bonding in organic compounds through the hybridization theory,classifications of organic compounds according to functional groups, nomenclature of organiccompounds, isomerism, chemical reactions, heterocyclic organic compounds, carbohydrates, amino acids and proteins, terpentines, application of organic compounds in medicine,agriculture and food industries .3.
  4. 4. Main Text Book ‫الكتاب الرئيسي المقرر‬ “Organic Chemistry”, T. W. ,Graham Solomons & Caring B. Fryhle; 10th ed, 2007. Subsidiary Books ‫الكتب المساعدة‬ “Organic Chemistry”, J. McMurry; 6th ed, 2003. “Organic Chemistry”, Mirison & Boyed; 6th ed, 1992.4
  5. 5. ‫مب‬ ‫رو‬ ‫كا‬ ‫توزيع الدرجات‬ ‫لتف‬ ‫وق‬ ‫51‬ ‫اختبار دوري أول‬ ‫01‬ ‫أنشطة‬ ‫51‬ ‫اختبار دوري ثاني‬ ‫02‬ ‫العملي‬ ‫04‬ ‫اختبار نهائي‬ ‫001 درجة‬ ‫المجموع النهائي‬‫5‬
  6. 6. Chapter 1Carbon Compounds and Chemical Bonds
  7. 7. Organic compounds are Inorganic compounds arecompounds that could be compounds that came fromobtained from living organisms. nonliving sources.
  8. 8. Introduction of Organic ChemistryThe chemistry of the compounds of carbon.The human body is largely composed of organiccompounds.Organic chemistry plays a central role in medicine,bioengineering etc.
  9. 9. Common Elements in Organic Compounds
  10. 10. Vitalism • It was originally thought organic compounds could be made only by living things by intervention of a “vital force”. • Fredrich Wöhler disproved vitalism in 1828 by making the organic compound urea from the inorganic salt ammonium cyanate by evaporation:
  11. 11. 11
  12. 12. The structure of atom Simplified structure of an atomstructure of carbon atom
  13. 13. – Isomers • Isomers are different molecules with the same molecular formula • Many types of isomers exist • Example – Consider two compounds with molecular formula C2H6O – These compounds cannot be distinguished based on molecular formula; however they have different structures – The two compounds differ in the connectivity of their atoms Chapter 1 13
  14. 14. – Constitutional Isomers • Constitutional isomers are one type of isomer • They are different compounds that have the same molecular formula but different connectivity of atoms • They often differ in physical properties (e.g. boiling point, melting point, density) and chemical properties Chapter 1 14
  15. 15. – Three Dimensional Shape of Molecules • Virtually all molecules possess a 3-dimensional shape which is often not accurately represented by drawings • It was proposed in 1874 by van’t Hoff and le Bel that the four bonds around carbon where not all in a plane but rather in a tetrahedral arrangement i.e. the four C-H bonds point towards the corners of a regular tetrahedron Chapter 1 15
  16. 16.  Electronegativity Electronegativity is the ability of an atom to attract electrons It increases from left to right and from bottom to top in the periodic table (noble gases excluded) Fluorine is the most electronegative atom and can stabilize excess electron density the best Chapter 1 16
  17. 17. Electronegativity is the ability of an atom to attract electrons. δ+ δ– δ0 δ0 H Cl H H
  18. 18. Electronegativities of Elements a se in cre in c rea se
  19. 19.  Resonance Often a single Lewis structure does not accurately represent the true structure of a molecule The real carbonate ion is not represented by any of the structures 1,2 or 3 Experimentally carbonate is known not to have two carbon- oxygen single bonds and one double bond; all bonds are equal in length and the charge is spread equally over all three oxygens Chapter 1 19
  20. 20. The real carbonate ion can be represented by a drawing inwhich partial double bonds to the oxygens are shown andpartial negative charge exists on each oxygenThe real structure is a resonance hybrid or mixture of allthree Lewis structuresDouble headed arrows are used to show that the three Lewisstructures are resonance contributors to the true structure The use of equilibrium arrows is incorrect since the three structures do not equilibrate; the true structure is a hybrid (average) of all three Lewis structures Chapter 1 20
  21. 21. One resonance contributor is converted to another by theuse of curved arrows which show the movement of electrons The use of these arrows serves as a bookkeeping device to assure all structures differ only in position of electronsA calculated electrostatic potential map of carbonate clearlyshows the electron density is spread equally among thethree oxygens Areas which are red are more negatively charged; areas of blue have relatively less electron density Chapter 1 21
  22. 22.  Rules for Resonance: Individual resonance structures exist only on paper The real molecule is a hybrid (average) of all contributing forms Resonance forms are indicated by the use of double-headed arrows Only electrons are allowed to move between resonance structures The position of nuclei must remain the same Only electrons in multiple bonds and nonbonding electrons can be moved Example: 3 is not a resonance form because an atom has moved All structures must be proper Lewis structures Chapter 1 22
  23. 23. The energy of the actual molecule is lower than the energyof any single contributing form The lowering of energy is called resonance stabilizationEquivalent resonance forms make equal contributions to thestructure of the real molecule Structures with equivalent resonance forms tend to be greatly stabilized Example: The two resonance forms of benzene contribute equally and greatly stabilize itUnequal resonance structures contribute based on theirrelative stabilities More stable resonance forms contribute more to the structure of the real molecule Chapter 1 23
  24. 24.  Rules to Assign Relative Importance of Resonance Forms A resonance form with more covalent bonds is more important than one with less Example: 6 is more stable and more important because it has more total covalent bonds Resonance forms in which all atoms have a complete valence shell of electrons are more important Example: 10 is more important because all atoms (except hydrogen) have complete octets Chapter 1 24
  25. 25. Resonance forms with separation of charge are lessimportant Separation of charge cost energy and results in a less stable resonance contributor Example: 12 is less important because it has charge separationForms with negative charge on highly electronegative atomsare more important Those with positive charge on less electronegative atoms are also more important Chapter 1 25
  26. 26.  Example The nitrate ion is known to have all three nitrogen-oxygen bond lengths the same and the negative charge spread over all three atoms equally Resonance theory can be used to produce three equivalent resonance forms Curved arrows show the movement of electrons between forms When these forms are hybridized (averaged) the true structure of the nitrate ion is obtained Chapter 1 26
  27. 27. Chemical Bonds: The Octet Rule Octet Rule •Atoms form bonds to produce the electronconfiguration of a noble gas (because the electronicconfiguration of noble gases is particularly stable). •For most atoms of interest this means achieving avalence shell configuration of 8 electronscorresponding to that of the nearest noble gas. •Atoms close to helium achieve a valence shellconfiguration of 2 electrons. •Atoms can form either ionic or covalent bonds tosatisfy the octet rule.
  28. 28. Chemical bondsA chemical bond is a force of attraction that holds two atomstogether to fill its electron shells with 8 electrons (octet rule). 1. Ionic bonds – 2. Covalent bonds – 3. Metallic bonds 28
  29. 29. IONIC BONDbond formed between two ions bythetransfer of electrons29
  30. 30. 1- The Ionic Bond is the electrostatic force that holds cations and anions together to form an ionic bonds. cation anion30
  31. 31. Ionic bond Li (metal) F (nonmetal) 2 2 1 131
  32. 32. COVALENT BONDbond formed by the sharing ofelectronsBonds in all the polyatomic ions and diatomics are allcovalent bonds32
  33. 33. Covalent Bond Covalent bonds occur between atoms of similar electronegativity (close to each other in the periodic table) H2
  34. 34.  Covalent Bonds Non polar covalent Bond Atoms achieve octets by sharing of valence electrons Molecules result from this covalent bonding Valence electrons can be indicated by dots (electron- dot formula or Lewis structures) but this is time- consuming The usual way to indicate the two electrons in a bond is to use a line (one line = two electrons ) Chapter 1 34
  35. 35. 2-Polar covalent bond or polar bond is a covalent bond with greater electron densityaround one of the two atoms electron rich electron poor region region e- poor e- rich H F H F δ+ δ-35 9.5
  36. 36.  Atomic Orbitals (AOs) The physical reality of Ψ is that when squared ( Ψ 2 ) it gives the probability of finding an electron in a particular location in space Plots of Ψ 2 in three dimensions generate the shape of s, p, d and f orbitals Only s and p orbitals are very important in organic chemistry Orbital: a region in space where the probability of finding an electron is large The typical representation of orbitals are those volumes which contain the electron 90-95% of the time Chapter 1 36
  37. 37.  Molecular Orbitals (MOs) A simple model of bonding is illustrated by forming molecular H 2 from H atoms and varying distance: Region I: The total energy of two isolated atoms Region II: The nucleus of one atom starts attracting the electrons of the other; the energy of the system is lowered Region III: at 0.74 Å the attraction of electrons and nuclei exactly balances repulsion of the two nuclei; this is the bond length of H 2 Region IV: energy of system rises as the repulsion of the two nuclei predominates Chapter 1 37
  38. 38. This simple model of bonding does not take intoaccount the fact that electrons are not stationary butconstantly moving aroundHeisenberg uncertainty principle: the position andmomentum of an electron cannot simultaneously beknownQuantum mechanics solves this problem by talkingabout the probability ( Ψ 2 ) of finding an electron at acertain location in spaceAs two atoms approach each other their atomicorbitals (AOs) overlap to become molecular orbitals(MOs)The wave functions of the AOs are combined to yieldthe new wave functions of the MOsThe number of MOs that result must always equal thenumber of AOs used Chapter 1 38
  39. 39.  Example: H 2 molecule As the hydrogen atoms approach each other their 1 s orbitals ( Ψ 1s) begin to overlap The MOs that form encompass both nuclei The electrons are not restricted to the vicinity of one nucleus or another Each MO has a maximum of 2 spin-paired electrons Addition of wave functions of the two atoms leads to a bonding molecular orbital Subtraction of wave functions of the two atoms leads to an anti-bonding molecular orbital The mathematic operation by which wave functions are added or subtracted is called the linear combination of atomic orbitals (LCAO) Chapter 1 39
  40. 40. Molecular Orbital of HydrogenØ atomic orbitalΨ+ and Ψ- molecular orbital = Ø1 ± Ø2 Ψ- = Ø1 - Ø2 antibonding orbital Ø1 Ø2 Ψ+ = Ø1 + Ø2 bonding orbital
  41. 41.  Bonding Molecular Orbitals ( Ψ molec ) AOs combine by addition (the AOs of the same phase sign overlap) The wave functions reinforce The value of Ψ increases between the two nuclei The value of Ψ 2 (electron probability density) in the region between the two nuclei increases The two electrons between the nuclei serve to attract the nuclei towards each other This is the ground state (lowest energy state) of the MO Chapter 1 41
  42. 42. Bonding Molecular OrbitalThe overlapping of two hydrogen 1s atomic orbitals 1s 1s Ø1 Ø2 Ψ+ = Ø1 + Ø2 atomic orbital atomic orbital bonding orbitalThe overlapping of two hydrogen 1s waves
  43. 43.  Antibonding molecular orbital ( Ψ * molec ) Formed by interaction of AOs with opposite phase signs Wave functions interfere and a node is produced ( Ψ = 0) In the region between the two nuclei A node is produced On either side of the node Ψ is small Ψ 2 (electron probability density) is small Electrons in the antibonding orbital avoid the region between the two nuclei Repulsive forces between the nuclei predominate and electrons in antibonding orbitals make nuclei fly apart Chapter 1 43
  44. 44. Antibonding Molecular OrbitalThe overlapping of two hydrogen 1s atomic orbitals 1s 1s Ø1 Ø2 Ψ- = Ø1 - Ø2 atomic orbital atomic orbital antibonding orbitalThe overlapping of two hydrogen 1s waves node
  45. 45. The energy of electrons in the bonding orbitals issubstantially less than the energy of electrons in theindividual atomsThe energy of electrons in the antibonding orbitals issubstantially moreIn the ground state of the hydrogen molecule electronsoccupy the lower energy bonding orbital only Chapter 1 45
  46. 46. Hybridization – is the mixing of two or more atomicorbitals in an atom (usually central atom) to form anew set of hybrid orbitals (same in shape andenergy). Mix at least 2 nonequivalent atomic orbitals (e.g. s and p). Hybrid orbitals have different shape and energy from original atomic orbitals. Number of hybrid orbitals is equal to the number of pure atomic orbitals used in the hybridization process. Covalent bonds are formed by: a. Overlap of hybrid orbitals with atomic orbitals b. Overlap of hybrid orbitals with other hybrid orbitals 10.4
  47. 47.  The Structure of Methane and Ethane: sp 3 Hybridization The structure of methane with its four identical tetrahedral bonds cannot be adequately explained using the electronic configuration of carbon Hybridization of the valence orbitals (2 s and 2p) provides four new identical orbitals which can be used for the bonding in methane Orbital hybridization is a mathematical combination of the 2 s and 2p wave functions to obtain wave functions for the new orbitals Chapter 1 47
  48. 48. When one 2s orbital and three 2p orbitals are hybridizedfour new and identical sp3 orbitals are obtainedWhen four orbitals are hybridized, four orbitals must resultEach new orbital has one part s character and 3 parts pcharacterThe four identical orbitals are oriented in a tetrahedralarrangementsThe antibonding orbitals are not derived in the followingdiagramThe four sp3 orbitals are then combined with the 1 s orbitalsof four hydrogens to give the molecular orbitals of methaneEach new molecular orbital can accommodate 2 electrons Chapter 1 48
  49. 49. sp3 hybridization in Methane CH4 excitation becomes Ground state excited state
  50. 50. Chapter 1 50
  51. 51. An sp3 orbital looks like a p orbital with one lobe greatlyextended Often the small lobe is not drawnThe extended sp 3 lobe can then overlap well with thehydrogen 1s to form a strong bondThe bond formed is called a sigma ( σ) bond because it iscircularly symmetrical in cross section when view along thebond axis Chapter 1 51
  52. 52. A variety of representations of methane show its tetrahedralnature and electron distribution a. calculated electron density surface b. ball-and-stick model c. a typical 3- dimensional drawing Chapter 1 52
  53. 53. Molecule geometry of CH4 4 sp3 hybrid orbitals 10.4
  54. 54.  Ethane (C 2 H 6 ) The carbon-carbon bond is made from overlap of two sp3 orbitals to form a σ bond The molecule is approximately tetrahedral around each carbon Chapter 1 54
  55. 55. The representations of ethane show the tetrahedralarrangement around each carbon a. calculated electron density surface b. ball-and-stick model c. typical 3- dimensional drawingGenerally there is relatively free rotation about σ bonds Very little energy (13-26 kcal/mol) is required to rotate around the carbon- carbon bond of ethane Chapter 1 55
  56. 56. Examples of Sigma Bond Formation56
  57. 57. The C—C σ Bond in Ethane The C—C σ Bond in EthaneIn-phase overlap of half-filled sp3 hybridorbital of one carbon with half-filled sp3hybrid orbital of another.Overlap is along internuclear axis to give a σ bond.
  58. 58. The C—C σ Bond in Ethane The C—C σ Bond in EthaneIn-phase overlap of half-filled sp3 hybridorbital of one carbon with half-filled sp3hybrid orbital of another.Overlap is along internuclear axis to give a σ bond.
  59. 59. hybrid orbitals – sp, sp2, or sp3
  60. 60. hybrid orbitals – sp, sp2, or sp3
  61. 61. formation of σ bond
  62. 62.  The Structure of Ethene (Ethylene) : sp 2 Hybridization Ethene (C 2 H 2 ) contains a carbon-carbon double bond and is in the class of organic compounds called alkenes Another example of the alkenes is propene The geometry around each carbon is called trigonal planar All atoms directly connected to each carbon are in a plane The bonds point towards the corners of a regular triangle The bond angle are approximately 120 o Chapter 1 63
  63. 63. There are three σ bonds around each carbon of ethene andthese are formed by using sp2 hybridized orbitalsThe three sp2 hybridized orbitals come from mixing one sand two p orbitals One p orbital is left unhybridizedThe sp2 orbitals are arranged in a trigonal planararrangement The p orbital is perpendicular (orthoganol) to the plane Chapter 1 64
  64. 64. Overlap of sp2 orbitals in ethylene results in formation of a σframework One sp2 orbital on each carbon overlaps to form a carbon-carbon σ bond; the remaining sp 2 orbitals form bonds to hydrogenThe leftover p orbitals on each carbon overlap to form abonding π bond between the two carbonsΑ π bond results from overlap of p orbitals above and belowthe plane of the σ bond It has a nodal plane passing through the two bonded nuclei and between the two lobes of the π molecular orbital Chapter 1 65
  65. 65. sp2 hybridization in Ethene C 2 H 4energy
  66. 66. sp2 hybridization in Ethene C 2 H 4 120 0
  67. 67. The bonding π orbital results from overlap of p orbital lobesof the same signThe antibonding π* orbital results from overlap of p orbitallobes of opposite sign The antibonding orbital has one node connecting the two nuclei and another node between the two carbonsThe bonding π orbital is lower in energy than theantibonding orbital In the ground state two spin paired electrons are in the bonding orbital The antibonding π*orbital can be occupied if an electron becomes promoted from a lower level ( e.g. by absorption of light) Chapter 1 69
  68. 68. The σ orbital is lower in energy than the π orbitalThe ground state electronic configuration of ethene is shown Chapter 1 70
  69. 69. σ bondremaining p orbitals from sp or sp2
  70. 70. π bond hinders rotation Planar molecule (each carbonabout the carbon-to- is trigonal planar) with π cloudcarbon bond above and below the plane formation of π bond
  71. 71.  Restricted Rotation and the Double Bond There is a large energy barrier to rotation (about 264 kJ/mol) around the double bond This corresponds to the strength of a π bond The rotational barrier of a carbon-carbon single bond is 13-26 kJ/mol This rotational barrier results because the p orbitals must be well aligned for maximum overlap and formation of the π bond Rotation of the p orbitals 90 o totally breaks the π bond Chapter 1 75
  72. 72.  Cis-trans isomers Cis-trans isomers are the result of restricted rotation about double bonds These isomers have the same connectivity of atoms and differ only in the arrangement of atoms in space This puts them in the broader class of stereoisomers The molecules below do not superpose on each other One molecule is designated cis (groups on same side) and the other is trans (groups on opposite side) Cis-trans isomerism is not possible if one carbon of the double bond has two identical groups Chapter 1 76
  73. 73.  The Structure of Ethyne (Acetylene): sp Hybridization Ethyne (acetylene) is a member of a group of compounds called alkynes which all have carbon-carbon triple bonds Propyne is another typical alkyne The arrangement of atoms around each carbon is linear with bond angles 180 o Chapter 1 77
  74. 74. The carbon in ethyne is sp hybridized One s and one p orbital are mixed to form two sp orbitals Two p orbitals are left unhybridizedThe two sp orbitals are oriented 180 o relative to each otheraround the carbon nucleus The two p orbitals are perpendicular to the axis that passes through the center of the sp orbitals Chapter 1 78
  75. 75. In ethyne the sp orbitals on the two carbons overlap to forma σ bond The remaining sp orbitals overlap with hydrogen 1s orbitalsThe p orbitals on each carbon overlap to form two π bondsThe triple bond consists of one σ and two π bonds Chapter 1 79
  76. 76. Depictions of ethyne show that the electron density aroundthe carbon-carbon bond has circular symmetry Even if rotation around the carbon-carbon bond occurred, a different compound would not result Chapter 1 80
  77. 77.  Bond Lengths of Ethyne, Ethene and Ethane The carbon-carbon bond length is shorter as more bonds hold the carbons together With more electron density between the carbons, there is more “glue” to hold the nuclei of the carbons together The carbon-hydrogen bond lengths also get shorter with more s character of the bond 2s orbitals are held more closely to the nucleus than 2 p orbitals A hybridized orbital with more percent s character is held more closely to the nucleus than an orbital with less s character The sp orbital of ethyne has 50% s character and its C-H bond is shorter The sp 3 orbital of ethane has only 25% s character and its C-H bond is longer Chapter 1 81
  78. 78. Bond length 1.53 1.34 1.2 Chapter 7 82 82
  79. 79.  Summary of Concepts from Quantum Mechanics  Atomic Orbital(AO): region in space around a nucleus where there is a high probability of finding an electron  Molecular Orbital (MO): results from overlap of atomic orbitals  Bonding Orbitals: when AOs of same sign overlap  Antibonding Orbitals: when AOs of opposite sign overlap  The energy of electrons in a bonding orbital is less than the energy of the individual atoms The energy of electronsChapter 1 in an antibonding orbitals is more 83
  80. 80.  The number of molecular orbitals formed equals the number of the atomic orbitals used Hybridized orbitals are obtained by mixing the wave functions of different types of orbitals Four sp 3 orbitals are obtained from mixing one s and three p orbitals The geometry of the four orbitals is tetrahedral This is the hybridization used in the carbon of methane Three sp2 orbitals are obtained from mixing one s and two p orbitals The geometry of the three orbitals is trigonal planar The left over p orbital is used to make a π bond This is the hybridization used in the carbons of ethene Two sp orbitals are obtained from mixing one s and one p orbital The geometry of the two orbitals is linear The two leftover p orbitals are used to make two π bonds This is the hybridization used in the carbons of ethyne Sigma (σ) bonds have circular symmetry when viewed along the bond axis Pi (π) bonds result from sideways overlap of two p orbitals Chapter 1 84
  81. 81.  Molecular Geometry: The Valence Shell Electron Pair Repulsion (VSEPR) M odel This is a simple theory to predict the geometry of molecules All sets of valence electrons are considered including: Bonding pairs involved in single or multiple bonds Non-bonding pairs which are unshared Electron pairs repel each other and tend to be as far apart as possible from each other Non-bonding electron pairs tend to repel other electrons more than bonding pairs do ( i.e. they are “larger”) The geometry of the molecule is determined by the number of sets of electrons by using geometrical principles Chapter 1 85
  82. 82.  Methane The valence shell of methane contains four pairs or sets of electrons To be as far apart from each other as possible they adopt a tetrahedral arrangement (bond angle 109.5 o) The molecule methane is therefore tetrahedral Chapter 1 86
  83. 83.  Ammonia When the bonding and nonbonding electrons are considered there are 4 sets of electrons The molecule is essentially tetrahedral but the actual shape of the bonded atoms is considered to be trigonal planar The bond angles are about 107 o and not 109.5 o because the non-bonding electrons in effect are larger and compress the nitrogen-hydrogen bond Chapter 1 87
  84. 84. Ammonia, NH 3 The electron pair geometry is tetrahedral. of electrons lone pair in tetrahedral position NH H HThe MOLECULAR GEOMETRY — thepositions of the atoms — is TRIGONALPYRAMID .
  85. 85.  Water There are four sets of electrons including 2 bonding pairs and 2 non-bonding pairs Again the geometry is essentially tetrahedral but the actual shape of the atoms is considered to be an angular arrangement The bond angle is about 105 o because the two “larger” nonbonding pairs compress the electrons in the oxygen- hydrogen bonds Chapter 1 89
  86. 86. Water, H2O The electron pair geometry The electron pair geometry is TETRAHEDRAL is TETRAHEDRAL ••H O H ••2 bond pairs2 lone pairs The molecular The molecular geometry is BENT.. geometry is BENT
  87. 87. Some Common Geometries Linear Trigonal Planar Tetrahedral
  88. 88. 92
  89. 89. What is the hybridization in each carbon atom? 4 2 5 6 3 7 1 sp3 – 2, 5 sp2 – 1, 3, 4 sp – 6, 7tetrahedral trigonal planar linear
  90. 90. What is the hybridization in each carbon atom? 4 3 2 1
  91. 91.  Representations of Structural Formulas Dot formulas are more cumbersome to draw than dash formulas and condensed formulas Lone-pair electrons are often (but not always) drawn in, especially when they are crucial to the chemistry being discussed Chapter 1 95
  92. 92.  Dash formulas Each dash represents a pair of electrons This type of representation is meant to emphasize connectivity and does not represent the 3-dimensional nature of the molecule The dash formulas of propyl alcohol appear to have 90 o angles for carbons which actually have tetrahedral bond angles (109.5 o) There is relatively free rotation around single bonds so the dash structures below are all equivalent Constitutional isomers Constitutional isomers have the same molecular formula but different connectivity Propyl alcohol (above) is a constitutional isomer of isopropyl alcohol (below) Chapter 1 96
  93. 93.  Condensed Structural Formulas In these representations, some or all of the dash lines are omitted In partially condensed structures all hydrogens attached to an atom are simply written after it but some or all of the other bonds are explicitly shown In fully condensed structure all bonds are omitted and atoms attached to carbon are written immediately after it For emphasis, branching groups are often written using vertical lines to connect them to the main chain Chapter 1 97
  94. 94.  Bond-Line Formulas A further simplification of drawing organic molecules is to completely omit all carbons and hydrogens and only show heteroatoms (e.g. O, Cl, N) explicitly Each intersection or end of line in a zig-zag represents a carbon with the appropriate amount of hydrogens Heteroatoms with attached hydrogens must be drawn in explicitly Chapter 1 98
  95. 95. Cyclic compounds are condensed using a drawing of thecorresponding polygonMultiple bonds are indicated by using the appropriatenumber of lines connecting the atoms Chapter 1 99
  96. 96.  Three-Dimensional Formulas Since virtually all organic molecules have a 3-dimensional shape it is often important to be able to convey their shape The conventions for this are: Bonds that lie in the plane of the paper are indicated by a simple line Bonds that come forward out of the plane of the paper are indicated by a solid wedge Bonds that go back out of the plane of the paper are indicated by a dashed wedge Generally to represent a tetrahedral atom: Two of the bonds are drawn in the plane of the paper about 109 o apart The other two bonds are drawn in the opposite direction to the in- plane bonds but right next to each other Chapter 1 100
  97. 97. Trigonal planar arrangements of atoms can be drawn in 3-dimensions in the plane of the paper Bond angles should be approximately 120 o These can also be drawn side-on with the central bond in the plane of the paper, one bond forward and one bond backLinear arrangements of atoms are always best drawn in theplane of the paper Chapter 1 101